Hydrochloric Acid → 3-tert-Butyl-5-(chloromethyl)-2-hydroxybenzaldehyde

HRID 919200Notes

Reaction equation

HRID 919200 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][CH:10]=[C:7](C=O)[C:6]=1[OH:13])([CH3:4])([CH3:3])[CH3:2].[CH2:14]=[O:15].[ClH:16].[C:17]([O-])([O-])=O.[Na+].[Na+]>>[C:1]([C:5]1[CH:12]=[C:11]([CH2:17][Cl:16])[CH:10]=[C:7]([CH:14]=[O:15])[C:6]=1[OH:13])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 4

HCID 313Hydrochloric Acid2×HCID 712FormaldehydeHCID 10340Sodium CarbonateHCID 36786753-tert-Butyl-2-hydroxybenzaldehyde

Product 1

HCID 158215393-tert-Butyl-5-(chloromethyl)-2-hydroxybenzaldehydeYield 97%

Procedure

A mixture of 3-tert-butylsalicylaldehyde (4)(3.56 g, 20 mmol) and paraformaldehyde (1.20 g, 40 mmol) was stirred with concentrated HCl (15 mL) for 14 days, although with the first drops of concentrated HCl, the emulsion became red. The mixture was then neutralized by treatment with a saturated solution of Na2CO3. The mixture was extracted with EtOAc (3×30 mL). Organic layers were dried over MgSO4 and the volatiles were evaporated under low pressure to give a beige solid which did not require further purification. Yield: 97%. Beige to red solid. 1H-NMR δH: 1.43 (9H, s, 3×CH3), 4.59 (2H, s, CH2), 7.43 (1H, d, J=2.1 Hz, HAr), 7.52 (1H, d, J=2.1 Hz, HAr), 9.87 (1H, s, CHO), 11.86 (1H, s, OH).

Workup

  1. extractionThe mixture was extracted with EtOAc (3×30 mL)
  2. dry with materialOrganic layers were dried over MgSO4
  3. customthe volatiles were evaporated under low pressure
  4. customto give a beige solid which
  5. custompurification

Sources & evidence

ORD record
ord-f16f0c0a265b40e88d8649038d050aa9
Source dataset
uspto-grants-2016_03
Patent number
US09273024B2

Reaction notes

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