Benzoyl chloride → 4-Hydroxy-3,3-dimethylbutyl benzoate

HRID 2170264Notes

Reaction equation

HRID 2170264 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][C:11]([CH3:17])([CH2:14][CH2:15][OH:16])[CH2:12][OH:13].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl>[C:1]([O:16][CH2:15][CH2:14][C:11]([CH3:17])([CH3:10])[CH2:12][OH:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 108878792,2-Dimethylbutane-1,4-diol

Product 1

HCID 669274344-Hydroxy-3,3-dimethylbutyl benzoateYield 44%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Benzoyl chloride (3.13 mL) was added to a cooled (−78° C.) solution of 2,2-dimethylbutane-1,4-diol from Step 1 (3.18 g), triethylamine (7.5 mL) and 4-(dimethylamino)pyridine (0.05 g) in dichloromethane (100 mL). The mixture was then slowly warmed up to room temperature and stirred overnight. The reaction mixture was concentrated in vacuo and the compound was purified by silica gel chromatography (hexanes/ethyl acetate 95:5 to 60:40) to afford 3,3-dimethyl-4-hydroxy-1-butyl benzoate (2.6 g, 44% yield) as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe compound was purified by silica gel chromatography (hexanes/ethyl acetate 95:5 to 60:40)

Sources & evidence

ORD record
ord-612d9fc089db48008d755b0f207530d7
Source dataset
uspto-grants-2015_06
Patent number
US09051248B2

Reaction notes

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