Formaldehyde → HCID 66879475, compound

HRID 69404Notes

Reaction equation

HRID 69404 reaction equation
[CH2:1]([O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[C:8]([CH3:15])[CH:7]=1)[CH2:2][CH2:3][CH3:4].[Li+].CC([N-]C(C)C)C.C(NC(C)C)(C)C.C([Li])CCC.[CH2:36]=[O:37]>C1COCC1.O>[CH2:1]([O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[C:8]([CH2:15][CH2:36][OH:37])[CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 5

HCID 712FormaldehydeHCID 7912DiisopropylamineHCID 2724682Lithium diisopropylamideHCID 534398994-Butoxy-2-methylbenzoic acidHCID 178418339Butyllithium

Product 1

HCID 66879475HCID 66879475, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-butoxy-2-methylbenzoic acid (2.5 g) in THF (15 mL) was added dropwise to a solution of LDA (freshly prepared from diisopropylamine (4.86 g) and n-butyllithium (32 mL; 1.5 M in hexane)) in THF (50 mL) at −78° C. After 10 minutes, paraformaldehyde (1.44 g) was added, and the mixture was allowed slowly to warm to room temperature. After 4 hours, water (10 mL) was added, and the volatile organic constituents were removed in a rotary evaporator. The residue was partitioned between water and diethyl ether. The aqueous phase was mixed with dichloromethane and cautiously acidified with hydrochloric acid at 0° C. Concentration of the organic phase afforded the desired product with the molecular weight of 238.29 (C13H18O4); MS (ESI): 239 (M+H+).

Workup

  1. waitAfter 4 hours
  2. customthe volatile organic constituents were removed in a rotary evaporator
  3. customThe residue was partitioned between water and diethyl ether
  4. additionThe aqueous phase was mixed with dichloromethane
  5. customcautiously acidified with hydrochloric acid at 0° C

Sources & evidence

ORD record
ord-9118a9284e894ee68070d5dc3106699a
Source dataset
uspto-grants-2014_09
Patent number
US08822495B2

Reaction notes

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