Acetic Acid → 5803-73-6

HRID 1460455Notes

Reaction equation

HRID 1460455 reaction equation
[BH4-].[Na+].[CH:3]1[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[CH:6]=[CH:5][C:4]=1[C:13](=[O:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15].C(O)(=O)C.O>C(O)C>[OH:19][CH:13]([C:4]1[CH:5]=[CH:6][C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=2[CH:3]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 133680115803-71-4

Product 1

HCID 133680145803-73-6Yield 99.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of sodium borohydride (2.0 g) in ethanol (100 ml) was added dropwise to an ice-cooled solution of ethyl 5,6,7,8-tetrahydro-2-naphthylglyoxylate (34.5 g) in ethanol (200 ml). After completion of dropwise addition, acetic acid (6 ml) was added and the reaction mixture was poured into water and extracted with chloroform. The chloroform layer was washed with water, dried (MgSO4) and the solvent was distilled off to give ethyl 2-hydroxy-(5,6,7,8-tetrahydro-2-naphthyl)acetate (34.5 g, yield 9%) as an oil.

Workup

  1. additionwas added
  2. extractionextracted with chloroform
  3. washThe chloroform layer was washed with water
  4. dry with materialdried (MgSO4)
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-4355ff7e551e4432a8519ed6de275ebd
Source dataset
uspto-grants-1991_12
Patent number
US05071841

Reaction notes

Loading…